SCS-C008119
11-demethyl-glucopiericidin A
Pathway: Polyketides
Glycoside
Chemical Structure
Loading 3D structure...
3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Source Information
Streptomyces psammoticus
(Streptomyces)
Original source name: Streptomyces psammoticus | S. psammoticus SCSIO NS126
Kingdom
Bacillati
Phylum
Actinomycetota
Class
Actinomycetes
Order
Kitasatosporales
Family
Streptomycetaceae
Genus
Streptomyces
Species
Streptomyces psammoticus
South China Sea
DOI:
10.3390/md19080428
· Marine Drugs
Drug-likeness (Lipinski Ro5)
Molecular Weight
563.7 Da
Threshold ≤ 500
ALogP
2.89
Threshold ≤ 5
H-Bond Donors
5
Threshold ≤ 5
H-Bond Acceptors
10
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C30H45NO9
Molecular Weight:
563.6880 Da
SMILES:
C/C=C/[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](C)/C=C(C)/C=C/C/C(C)=C/Cc1nc(OC)c(OC)c(O)c1C
InChIKey:
KTKZCQSYWPZNJB-NNLUNFTPSA-N
InChI:
InChI=1S/C30H45NO9/c1-8-10-22(39-30-27(36)26(35)25(34)23(16-32)40-30)19(4)15-18(3)12-9-11-17(2)13-14-21-20(5)24(33)28(37-6)29(31-21)38-7/h8-10,12-13,15,19,22-23,25-27,30,32,34-36H,11,14,16H2,1-7H3,(H,31,33)/b10-8+,12-9+,17-13+,18-15+/t19-,22+,23-,25-,26+,27-,30-/m1/s1
Calculated Properties
ALogP:
2.892 lipophilicity
TPSA:
150.96 Ų polar surface area
H-Bond Donors:
5
H-Bond Acceptors:
10
Rotatable Bonds:
13
Ring Count:
2
(1 aromatic)
Chiral Centers:
7
Fsp³:
0.5667 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008119
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
N/A
NPClassifier Class:
N/A
Glycoside:
Yes
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
Biological Activity Data
Activity values are displayed only when a quantitative or clearly reported result is available.
Tested organisms, cell lines and molecular targets are shown under Target / model.
| Activity | Assay | Target / model | Result | Reference |
|---|---|---|---|---|
| Antitumor | IC50 | ACHN cells | 2.3 μM | 10.3390/md19080428 Marine Drugs |
| Antitumor | IC50 | HL-60 cells | 1.3 μM | 10.3390/md19080428 Marine Drugs |
| Antitumor | IC50 | K562 cells | 5.5 μM | 10.3390/md19080428 Marine Drugs |
| Antitumor | — | S phase | 8 (2 μM, Figure 5C) could arrest the cell cycle during the S phase in HL-60 and ACHN cells. | 10.3390/md19080428 Marine Drugs |